As a method for producing substituted triazines, various methods have been known so far. It is reported, for example, a method in which a compound of the formula (III) ##STR1## wherein X.sup.4 and X.sup.5 each represent an diethylamino group and X.sup.6 represents an ethylamino group or X.sup.4 and X.sup.5 represent an amino group and X.sup.6 represents an ethylamino group or diethylamino group is produced by the reaction of 2-chloro-1,3,5-triazine with ethylamine (J. Amer. Chem. Soc., vol. 73, p. 2984, 1951).
It is reported a method in which a compound of the formula (III) wherein X.sup.4, X.sup.5 and X.sup.6 each represent an ethylamino group is produced by the reaction of 2,4,6-trimethylthio-1,3,5-triazine with ethylamine (Chem. Ber., vol. 18, p. 2755, 1885).
It is reported a method in which a compound of the formula (III) wherein X.sup.4 represents an amino group, X.sup.5 represents an amino group or an octylamino group, and X.sup.6 represents an octylamino group is produced by the reaction of 2,4,6-triamino-1,3,5-triazine with octylamine hydrochloride (U.S. Pat. No. 2,228,161, 1941).
It is reported a method in which a compound of the formula(III) wherein X.sup.4 represents a phenyl group, and X.sup.5 and X.sup.6 each represent a butylamino group is produced by the reaction of 2-phenyl-4,6-diamino-1,3,5-triazine with butylamine (U.S. Pat. No. 2,385,766, 1945). Further, 2,4,6-1,3,5-triazine derivatives produced from cyanuric chloride are used as a flame retardant of a thermoplastic polymer (Japanese Patent Application Laid-Open No. Hei 3-1215564). Specific examples of the derivatives described in this Japanese Patent Application Laid-open No. Hei 3-215564 are as follows as a part thereof. ##STR2##
Examples of reaction of aminotriazines with carbonyl compounds such as aldehydes or ketones are represented by the reaction example in which hydroxymethylation was conducted by melamine and an aqueous formalin solution under the weakly alkali condition. (J. Amer. Chem. Soc., vol. 69, p. 599, 1947).
The method described in J. Amer. Chem. Soc., vol. 73, p. 2984, 1954 requires a condensation agent in an amount of more than a stoichiometrical amount in many cases and causes formation of by-products such as salts and the like which is often industrially problematic. The method described in Chem. Ber., vol. 18, p. 2755, 1885 causes formation of by-products such as sulfur compounds and the like which is often industrially problematic. The methods described in U.S. Pat. No. 2,228,161 (1941) and U.S. Pat. No. 2,385,766 (1945) require high temperatures in the reaction. Besides, the former method causes formation of by-product ammonium chloride. Any of the above-mentioned methods conduct the substitution reaction with the leaving group by using substituted amines which are not said to be industrially inexpensive, and this is one of the reasons that substituted triazines cannot be supplied at low costs.
In the reactions of amino trizines with carbonyl compounds such as aldehydes or ketones, the reactivity of amino group in the triazine rings is low. Therefore, as described in J. Amer. Chem. Soc., vol. 69, p. 599, 1947, it is general to carry out the hydroxymethylation by the reaction with formaldehyde which has high reactivity with melamines. In a case of the reaction with other carbonyl compounds, especially, with aldehydes, it has been known such a reaction that an equilibrium mixture of a raw material and a hydroxy-alkylated compound is obtained and its product is unstable or a reaction under dehydration-condensation with further aminotriazines is easily conducted to obtain polynucleic compounds.